Potassium Carbonate → 6-(4-(2-(Benzylamino)ethyl)phenoxy)nicotinamide

HRID 228144

반응식

HRID 228144 반응식
Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=1.[CH2:11]([NH:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].CC(N(C)C)=O>C(CC(C)(C)C)(C)C>[CH2:11]([NH:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:2]2[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=2)=[CH:23][CH:22]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 804566-ChloronicotinamideHCID 30425724-(2-(Benzylamino)ethyl)phenol

생성물 1

HCID 444340576-(4-(2-(Benzylamino)ethyl)phenoxy)nicotinamide수율 127.9%

시약·촉매·용매 1

HCID 109072,2,4-Trimethylpentane용매

실험 절차

Add 6-chloronicotinamide (7.03 g, 44.90 mmol) to a stirred solution of 4-(2-benzylamino-ethyl)-phenol (10.10 g, 44.43 mmol), potassium carbonate (15.35 g, 111.1 mmol), dimethylacetamide (138 mL), and isooctane (16 mL). Using a Dean-Stark trap, heat the reaction to reflux under nitrogen for 6 h. Cool the reaction mixtures to room temperature, filter off the solids, and concentrate most of the solvent off on a rotary evaporator. Take the residue up in ethyl acetate (200 mL) and add 1N hydrochloric acid (200 mL). Stir for 15 minutes and filter off the precipitate washing with ethyl acetate. Dissolve the solid in 400 mL of boiling 1:1 methanol/water. To this solution add 5N sodium hydroxide (35 mL) and allow the solution to cool to room temperature. Filter and wash with water to yield 19.74 g (83%) of 6-[4-(2-benzylamino-ethyl)-phenoxy]-nicotinamide: mass spectrum (ion spray): m/z=348.1 (M+1); 1H NMR (CDCl3): 8.58 (d, 1H), 8.15 (dd, 1H), 7.34-7.24 (m, 7H), 7.06 (d, 2H), 6.93 (d, 1H), 6.08 (br s, 2H), 3.82 (s, 2H), 2.92 (t, 2H), 2.84 (t, 2H), 1.33 (br s, 1H).

후처리

  1. temperatureheat
  2. customthe reaction
  3. temperatureto reflux under nitrogen for 6 h
  4. temperatureCool the reaction
  5. custommixtures to room temperature
  6. filtrationfilter off the solids
  7. concentrationconcentrate most of the solvent off on a rotary evaporator
  8. additionadd 1N hydrochloric acid (200 mL)
  9. filtrationfilter off the precipitate
  10. washwashing with ethyl acetate
  11. dissolutionDissolve the solid in 400 mL
  12. additionTo this solution add 5N sodium hydroxide (35 mL)
  13. filtrationFilter
  14. washwash with water

출처 및 근거

ORD 기록
ord-844e854d0ed8488bbed28958a30574b2
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560463B2

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